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List of progestogens

Steroid ring system.

This is a list of progestogens that are or that have been used in clinical or veterinary medicine. They are steroids and include derivatives of progesterone and testosterone.

Progesterone derivatives

Compound Chemical name Structure
Progesterone Pregn-4-ene-3,20-dione Progesteron.svg
Quingestrone Progesterone 3-cyclopentyl enol ether Quingestrone.svg

Retroprogesterone derivatives

Compound Chemical name Structure
Retroprogesterone 9β,10α-Progesterone Retroprogesterone.svg
Dydrogesterone 6-Dehydro-9β,10α-progesterone Dydrogesterone.png
Trengestone 6-Chloro-1,6-didehydro-9β,10α-progesterone Trengestone.svg

Note that although an active progestogen, retroprogesterone is not medically used.

17α-Hydroxyprogesterone derivatives

Compound Chemical name Structure
Hydroxyprogesterone 17α-Hydroxyprogesterone 17-Hydroxyprogesterone.svg
Acetomepregenol (mepregenol diacetate) 3β,17α-Diacetoxy-6-methyl-6-dehydro-3-deketoprogesterone Acetomepregenol.svg
Algestone 16α,17α-Dihydroxyprogesterone Algestone.png
Algestone acetophenide 16α,17α-Dihydroxyprogesterone acetophenide Algestone acetophenide.png
Anagestone acetate 17α-Acetoxy-6α-methyl-3-deketoprogesterone Anagestone acetate.svg
Chlormadinone acetate 17α-Acetoxy-6-chloro-6-dehydroprogesterone Chlormadinone acetate.svg
Chlormethenmadinone acetate 17α-Acetoxy-6-chloro-16-methylene-6-dehydroprogesterone Chlormethenmadinone acetate.svg
Cyproterone acetate 17α-Acetoxy-1,2α-methylene-6-chloro-6-dehydroprogesterone Cyproterone acetate.svg
Delmadinone acetate 17α-Acetoxy-6-chloro-1,6-didehydro-progesterone Delmadinone acetate.svg
Flugestone acetate (flurogestone acetate) 17α-Acetoxy-9α-fluoro-11β-hydroxyprogesterone Flugestone acetate.svg
Flumedroxone acetate 17α-Acetoxy-6α-(trifluoromethyl)progesterone Flumedroxone acetate.svg
Hydroxyprogesterone acetate 17α-Acetoxyprogesterone 17-Acetoxyprogesterone.svg
Hydroxyprogesterone caproate 17α-Hexanoxyprogesterone Hydroxyprogesterone caproate.svg
Hydroxyprogesterone heptanoate 17α-Heptanoxyprogesterone Hydroxyprogesterone heptanoate.svg
Medroxyprogesterone acetate 17α-Acetoxy-6α-methylprogesterone Medroxyprogesterone 17-acetate.png
Megestrol acetate 17α-Acetoxy-6-methyl-6-dehydroprogesterone Megestrol acetate.svg
Melengestrol acetate 17α-Acetoxy-16-methylene-6-methyl-6-dehydroprogesterone Melengestrol acetate.png
Methenmadinone acetate 17α-Acetoxy-16-methylene-6-dehydroprogesterone Methenmadinone acetate.svg
Osaterone acetate 17α-Acetoxy-6-chloro-2-oxa-6-dehydroprogesterone Osaterone skeletal.svg
Pentagestrone acetate 17α-Acetoxyprogesterone 3-cyclopentyl enol ether Pentagestrone acetate.svg

Note that 17α-hydroxyprogesterone is inactive as a progestogen and is not used medically.

The 19-norprogesterone derivatives gestonorone caproate (gestronol hexanoate), nomegestrol acetate, segesterone acetate (nestorone, elcometrine), and norgestomet are also derivatives of 17α-hydroxyprogesterone (see below).

17α-Methylprogesterone derivatives

Compound Chemical name Structure
17α-Methylprogesterone 17α-Methylprogesterone Methylprogesterone.svg
Medrogestone 6,17α-Dimethyl-6-dehydroprogesterone Medrogestone.png

Note that although an active progestogen, 17α-methylprogesterone is not medically used.

The 19-norprogesterone derivatives demegestone, promegestone, and trimegestone are also derivatives of 17α-methylprogesterone (see below).

Other 17α-substituted progesterone derivatives

Compound Chemical name Structure
Haloprogesterone 6α-Fluoro-17α-bromoprogesterone Haloprogesterone.svg
Proligestone 14α,17α-Propylidenedioxyprogesterone Proligestone.svg

19-Norprogesterone derivatives

Compound Chemical name Structure
19-Norprogesterone 19-Norprogesterone 19-Norprogesterone.svg
Demegestone 17α-Methyl-9-dehydro-19-norprogesterone Demegestone.png
Gestonorone caproate (gestronol hexanoate) 17α-Caproxy-19-norprogesterone Gestronol caproate.svg
Nomegestrol acetate 17α-Acetoxy-6-methyl-6-dehydro-19-norprogesterone Nomegestrol acetate.svg
Norgestomet 17α-Acetoxy-11β-methyl-19-norprogesterone Norgestomet.svg
Promegestone 17α,21-Dimethyl-9-dehydro-19-norprogesterone Promegestone.png
Segesterone acetate (nestorone, elcometrine) 17α-Acetoxy-16-methylene-19-norprogesterone Nestorone.svg
Trimegestone 21β-Hydroxy-17α,21-dimethyl-9-dehydro-19-norprogesterone Trimegestone.png

Note that although an active progestogen, 19-norprogesterone is not medically used.

Testosterone derivatives

Compound Chemical name(s) Structure
Testosterone 17β-Deacetyl-17β-hydroxyprogesterone
Androst-4-en-17β-ol-3-one
Testosteron.svg

Note that testosterone itself does not have significant progestogenic activity. Testosterone is instead classified as an anabolic-androgenic steroid and is included here purely because it is the parent structure of this group of progestins.

17α-Ethynyltestosterone derivatives

Compound Chemical name(s) Structure
Ethisterone (ethinyltestosterone) 17α-Ethynyltestosterone Ethisterone.svg
Danazol (2,3-isoxazolethisterone) 2,3-Isoxazol-17α-ethynyltestosterone? Danazol.svg
Dimethisterone 6α,21-Dimethyl-17α-ethynyltestosterone Dimethisterone.png

19-Nortestosterone derivatives

Compound Chemical name(s) Structure
Nandrolone (nortestosterone) 19-Nortestosterone Nandrolone.svg
Oxendolone (TSAA-291) 16β-Ethyl-19-nortestosterone Oxendolone.svg

Note that while nandrolone (19-nortestosterone) does have significant progestogenic activity, it is not used as a progestogen. It is instead classified as an androgenic-anabolic steroid and is included here purely because it is an important parent structure of this group of progestins.

17α-Ethynyl-19-nortestosterone derivatives

Estranes

Compound Chemical name(s) Structure
Norethisterone (norethindrone) 17α-Ethynyl-19-nortestosterone Norethisterone.svg
Etynodiol diacetate (ethynodiol diacetate) 17α-Ethynyl-3-deketo-3β-hydroxy-19-nortestosterone 3β,17β-diacetate Ethynodiol diacetate.svg
Lynestrenol (3-deketonorethisterone) 17α-Ethynyl-3-deketo-19-nortestosterone Lynestrenol.svg
Norethisterone acetate (norethindrone acetate) 17α-Ethynyl-19-nortestosterone 17β-acetate Norethisterone acetate.svg
Norethisterone enanthate (norethindrone enanthate) 17α-Ethynyl-19-nortestosterone 17β-enanthate Norethindrone enanthate.svg
Noretynodrel (norethynodrel) 17α-Ethynyl-δ5(10)-19-nortestosterone Noretynodrel.svg
Norgestrienone (ethinyltrenbolone) 17α-Ethynyl-19-nor-δ9,11-testosterone Norgestrienone.svg
Quingestanol acetate 4-Hydro-17α-ethynyl-19-nor-δ3,5-testosterone 3-cyclopentyl ether 17β-acetate? Quingestanol acetate.svg
Tibolone (7α-methylnoretynodrel) 7α-Methyl-17α-ethynyl-19-nor-δ5(10)-testosterone Tibolone.svg

18-Methylestranes (13β-ethylgonanes)

Compound Chemical name(s) Structure
Desogestrel 3-Deketo-11-methylene-17α-ethynyl-18-methyl-19-nortestosterone Desogestrel.svg
Etonogestrel (3-ketodesogestrel) 11-Methylene-17α-ethynyl-18-methyl-19-nortestosterone Etonogestrel.svg
Gestodene (15-dehydronorgestrel) 17α-Ethynyl-18-methyl-19-nor-δ15-testosterone Gestodene.svg
Gestrinone (ethylnorgestrienone, R-2323) 17α-Ethynyl-18-methyl-19-nor-δ9,11-testosterone Gestrinone.svg
Levonorgestrel 17α-Ethynyl-18-methyl-19-nortestosterone Levonorgestrel.svg
Norelgestromin (17β-deacetylnorgestimate, norgestrel 3-oxime) 17α-Ethynyl-18-methyl-19-nortestosterone 3-oxime Norelgestromin.svg
Norgestimate 17α-Ethynyl-18-methyl-19-nortestosterone 3-oxime 17β-acetate Norgestimate.svg
Norgestrel (13-methylnorethisterone) rac-13-Ethyl-17α-ethynyl-19-nortestosterone Levonorgestrel.svg
Dextronorgestrel.svg

Other 17α-substituted 19-nortestosterone derivatives

Compound Chemical name(s) Structure
Allylestrenol (allyloestrenol) 3-Deketo-17α-allyl-19-nortestosterone Allylestrenol.svg
Altrenogest (allyltrenbolone, allyltrienolone) 17α-Allyl-19-nor-δ9,11-testosterone Altrenogest.svg
Dienogest 17α-Cyanomethyl-19-nor-δ9-testosterone Dienogest.svg
Normethandrone (methylestrenolone, normethandrolone, normethisterone, methylnortestosterone) 17α-Methyl-19-nortestosterone Methylestrenolone.svg
Norvinisterone (vinylnortestosterone, SC-4641) 17α-Vinyl-19-nortestosterone Norvinisterone.svg
Norgesterone (norvinodrel, vinylestrenolone, vinylnoretynodrel) 17α-Vinyl-δ5(10)-19-nortestosterone Norgesterone.svg

Spirolactone derivatives

Compound Chemical name(s) Structure
SC-5233 (spirolactone) 17α-(2-Carboxyethyl)testosterone γ-lactone SC-5233.svg
Drospirenone 6β,7β:15β,16β-Dimethylenespirolactone Drospirenone.svg

Note that although an active progestogen, SC-5233 (spirolactone) is not medically used.

See also

Notes

? = Chemical names that are unverified.

Further reading

  • McRobb L, Handelsman DJ, Kazlauskas R, Wilkinson S, McLeod MD, Heather AK (2008). "Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay". J. Steroid Biochem. Mol. Biol. 110 (1–2): 39–47. doi:10.1016/j.jsbmb.2007.10.008. PMID 18395441.